Controlled fragrance release from galactose-based pro-fragrances

Kuhnt, Tobias; Herrmann, Andreas; Benczédi, Dániel; Weder, Christoph; Foster, E. Johan

doi:10.1039/c4ra07728h

Cited by 16 publications

(30 citation statements)

References 32 publications

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“…[20][21][22][23][24]49 Dry βD-CNCs (100 mg) were mixed directly with the aqueous surfactant emulsion (1.8 g) and deionized water (1 mL) was added to permit better mixing. The mixtures were stirred for 10 min, transferred into 1 L beakers and diluted with deionized water (600 g).…”

Section: Deposition Of βD-cncs (3) and β-Damascone Reference Onto Cotmentioning

confidence: 99%

“…mers, a comparison of the above data with the release kinetics observed previously for monosaccharide-based pro-fragrances using the same release chemistry suggests similar release rates. 23 Dynamic headspace analysis of β-damascone released from ceramic tiles…”

Section: Release Of β-Damascone From βD-cncs In Aqueous Buffer Dispermentioning

confidence: 99%

“…[15][16][17][18][19][20][21][22] Based on the hypothesis that monosaccharide-based pro-fragrances adsorb well on cotton textiles, which is an important requirement for their use in laundry products, 20 we recently reported the investigation of new galactose-based pro-fragrances that were prepared by reacting δ-damascone in a 1,4-addition with mercaptoacetic acid and coupling this product with 1,2:3,4-di-O-isopropylidene-α-D-galactopyranose, which was optionally deprotected to a more hydrophilic variant. 23 Fragrance release occurred via a retro 1,4-Michael-type reaction over the course of days, at rates that were pH dependent, and at a level that represents an increase by over two orders of magnitude in comparison to the neat fragrance. Typically, the precursor is stable at acidic pH and releases the fragrance under neutral or alkaline conditions.…”

Section: Introductionmentioning

confidence: 99%

“…Typically, the precursor is stable at acidic pH and releases the fragrance under neutral or alkaline conditions. [22][23][24] In many cases, the application of personal care products is followed by rinsing with water, which dilutes the product and leads to neutralization of the pH. Therefore thioether pro-fragrances should be particularly suitable for acidic product formulations, because hydrolysis during the storage of the product is expected to be slow and the release of the fragrance preferentially occurs after application.…”

Section: Introductionmentioning

confidence: 99%

“…2,[42][43][44] We employed a short thioether linker that served to bind the fragrance molecules to the CNCs and permits their release under neutral or basic conditions via the previously explored retro 1,4-Michael-type reaction. [20][21][22][23][24] The release of β-damascone from the CNC-based pro-fragrances was studied in aqueous suspension as a function of pH, and after deposition of the nanoparticles onto different substrates under conditions that emulate the use in laundry applications as well as in an all-purpose surface cleaner.…”

Section: Introductionmentioning

confidence: 99%

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Functionalized cellulose nanocrystals as nanocarriers for sustained fragrance release

et al. 2015

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The desire to extend the release time of highly volatile scents has led to the development of different types of fragrance release systems. We here report a new family of nanocarrier-based pro-fragrances, which have a high affinity to cotton textiles and release their payload under everyday life conditions. The new release systems were created by decorating cellulose nanocrystals (CNCs) with β-damascone, using a short linker that serves to bind the fragrance molecules to the CNC surface and permits their slow release via a retro 1,4-Michael-type reaction. The fragrance release was investigated in aqueous suspensions by gas chromatography coupled to mass spectrometry as a function of pH; the data show that the new pro-fragrances are stable under acidic conditions, but release the β-damascone at basic pH. The chemical resemblance of the CNCs and cotton was thought to be beneficial in terms of adhesion of the nanocarriers on textile substrates, which is an important requirement for the use of pro-fragrances in laundry applications. Thus, the deposition of the new pro-fragrances onto cotton and subsequent fragrance release were probed by dynamic headspace analysis in combination with gas chromatography. The data show that β-damascone is indeed slowly released, and that the quantity of fragrance released after 3 days is up to 80 times higher than in the case of reference experiments, where the tissue was treated with the neat fragrance under identical conditions. † Electronic supplementary information (ESI) available: NMR, IR spectra, gas chromatograms and TGA data. See

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Section: Deposition Of βD-cncs (3) and β-Damascone Reference Onto Cotmentioning

confidence: 99%

Section: Release Of β-Damascone From βD-cncs In Aqueous Buffer Dispermentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Functionalized cellulose nanocrystals as nanocarriers for sustained fragrance release

et al. 2015

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Preparation of polyacrylate/paraffin microcapsules and its application in prolonged release of fragrance

Zhang

Song

Chen

2016

J of Applied Polymer Sci

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The purpose of the present work was to develop a fragrance encapsulation system using polyacrylate/paraffin microcapsules. The polyacrylate/paraffin microcapsules were fabricated by the method of suspension polymerization in Pickering emulsion. Morphology, size distribution, and thermal resistance of polyacrylate/paraffin microcapsules were investigated by scanning electron microscopy, light scattering particle size analyzer, and thermogravimetric analyzer. Results indicated that the crosslinked PMMA/ paraffin microcapsules and P(MMA-co-BMA)/paraffin microcapsules prepared under optimal conditions presented regular spherical shape and similar size distribution. The crosslinked P(MMA-co-BMA)/paraffin microcapsules exhibited better thermal stability, with a thermal resistance temperature up to 184 8C. Fragrance microcapsules were prepared by encapsulating fragrance into crosslinked P(MMA-co-BMA)/paraffin microcapsules. The prolonged release performance of fragrance microcapsules was measured by ultravioletvisible near-infrared spectrophotometer. 63.9% fragrance was retained after exposing fragrance microcapsules in air for 3 months, and the fragrance continued to release over 96 h in surfactant solution (sodium lauryl sulfonate, 20 wt %). V C 2016 Wiley Periodicals, Inc. J.Appl. Polym. Sci. 2016, 133, 44136.

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Preparation of aroma microcapsules with sodium alginate and tetradecylallyldimethylammonium bromide (TADAB) and its potential applications in cosmetics

Song

Chen

2017

Flavour & Fragrance J

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The formation of apple aroma microcapsules was achieved by sodium alginate (SA) and tetradecylallydimethylammonium bromide (TADAB) as shells based on complex coacervation‐emulsion polymerization. Alkyl alcohol polyoxyethylene ether was employed as emulsifier. Pentaerythritol tetraacrylate (PETRA) was used as a crosslinking agent and methyl methacrylate (MMA) was applied as comonomer to copolymerize with TADAB. The aroma microcapsules were characterized by scanning electron microscopy (SEM). Results showed that the aroma microcapsules prepared under optimal conditions were core‐shell structure. The aroma microcapsules were sphere‐like shape with particle size between 20 to 50 μm. FT‐IR analysis results showed that the electrostatic interactions and polymerization occurred assuredly. TG‐DTA study indicated that the thermal stability of the aroma microcapsules crosslinked with MMA shell was improved, and the thermal resistant temperature was up to 110°C. Moreover, the encapsulation efficiency of aroma microcapsules was measured by ultraviolet–visible near‐infrared spectrophotometer. In the surfactant solution, the release of aroma was quick during the first 8 hours, losing ca. 10.8% aroma encapsulated, however, there was no more else aroma dissolving out from the 9th hour. In open conditions, the encapsulation efficiency of the aroma microcapsules kept 66.57% after 48 hours, compared with the encapsulation efficiency going down alone if the microcapsules were milled.

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Controlled fragrance release from galactose-based pro-fragrances

Abstract: Conjugating α,β-unsaturated ketonesviaa thioether linkage to carbohydrates is an efficient way to modulate the polarity of the precursors and thus to influence the release of damascones in functional perfumery.

Cited by 16 publications

References 32 publications

Functionalized cellulose nanocrystals as nanocarriers for sustained fragrance release

Functionalized cellulose nanocrystals as nanocarriers for sustained fragrance release

Preparation of polyacrylate/paraffin microcapsules and its application in prolonged release of fragrance

Preparation of aroma microcapsules with sodium alginate and tetradecylallyldimethylammonium bromide (TADAB) and its potential applications in cosmetics

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